Patent GB-558433-A (GB)
Title: New anthraquinone dyestuffs
IPC: C09B62/80
Filed: 1942-07-01
Abstract: 558,433. Dyes. BUCKLEY, G. D., TATUM, W. W., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. July 1, 1942, No. 9052. [Classes 2 (iii) and 15 (ii)] Dyes of the general formula wherein A represents a straight-chain alkylene radicle of 2 or 3 carbon atoms and X represents H, an alkali metal or NH  4 , are obtained by treating with a sulphonating agent (a) a 1- amino-4-hydroxyanthraquinone carrying in 2- position a group -OAOAlkyl, or (b) the reaction product of a 1-amino-4-hydroxyanthraquinone, carrying in 2-position an aryloxy group, a halogen atom, a sulphonic acid group or an alkoxy (C 1  to C 5 ) group, with a solution of an alkali metal or an alkali metal hydroxide in a dihydric alcohol containing 2 or 3 carbon atoms, the products being converted in each case, if desired, into the alkali metal or ammonium salts. The products give on cellulose acetate artificial silk brilliant red shades fast to light and to washing and on animal fibres, e.g. wool, from an acid bath, fast level bright red shades. In examples (1) 1-amino-4-hydroxy-2-phenoxyanthraquinone is added to trimethylene glycol containing caustic potash and pyridine, the mixture is boiled under reflux for 16 hours and the product, after purification, is sulphated by treatment for 1 hour with 100 per cent. sulphuric acid at 15‹ C. and converted into the sodium salt by reaction with sodium carbonate; (2) 1-amino-4-hydroxy-2-phenoxy-anthraquinone is added to ethylene glycol containing caustic potash, the mixture is stirred for 16 hours at 120-125‹ C. and the product, after purification, is sulphated by stirring for 2 hours with sodium pyrosulphate in pyridine at 95- 100‹ C. and converted into the sodium salt as in (1) ; (3) 1-amino-4-hydroxy-2-bromoanthraquinone is added with phenol to ethylene glycol containing caustic potash, the mixture is stirred for 18 hours at 145-150‹ C. and the product is converted as in (2) into the sodium salt of its sulphuric acid ester ; (4) sodium 1-amino-4- hydroxyanthraquinone-2-sulphonate is added to ethylene glycol containing caustic potash and pyridine, the mixture is stirred for 16 hours at 125‹ C. and the product, after purification, is converted as in (2) into the sodium salt of its sulphuric acid ester; (5) 1-amino-4-hydroxy- 2-#-ethoxyethoxyanthraquinone is stirred at 20-30‹ C. with a mixture of 100 per cent. sulphuric acid and oleum and the product is converted into the sodium salt by reaction with sodium carbonate; the corresponding #- methoxyethoxy or #-n-butoxyderivative may be used in place of the #-ethoxyethoxy derivative ; (6) 1-amino-4-hydroxy-2-γ-ethoxypropoxyanthraquinone is similarly treated with sulphuric acid and oleum. 1- Amino - 4 - - hydroxy - 2 - phenoxyanthraquinone is obtained by heating 1-amino-4- hydroxy-2-bromoanthraquinone with phenol caustic potash. 1- Amino - 4 - hydroxy - 2 - # - methoxy-, ethoxy-, or n-butoxy-ethoxyanthraquinone is obtained by heating 1-amino-4-hydroxy-2- phenoxyanthraquinone, with ethylene glycol monomethyl, monoethyl or mono-n-butyl ether and respectively and caustic potash. 1 - Amino - 4 - - hydroxy - 2 - γ - ethoxypropoxyanthraquinone is obtained by heating 1- amino-4-hydroxy-2-phenoxyanthraquinone with 1:3-propylene glycol monoethyl ether and caustic potash.